Polysulfide modified epoxy resins

Abstract

This invention relates to polysulfide modified epoxy resins with enhanced physical and mechanical properties. The composition comprises the copolymerization product of epoxy resins and (vinylaryl)alkyl substituted polysulfides. Such compositions are useful in coating formulations and structural and electrical applications.

What is claimed is: 
     
       1. A polysulfide modified epoxy resin composition comprising the copolymerization product of an epoxy resin, a (vinylaryl)alkyl substituted polysulfide, and a polymerizable ethylenically unsaturated compound. 
     
     
       2. The polysulfide modified epoxy resin of claim 1 wherein the ethylenically unsaturated compound comprises compounds capable of copolymerization with monomers having terminal or pendant, vinyl-reactive olefinic or cycloolefinic double bonds. 
     
     
       3. The polysulfide modified epoxy resin of claim 2 wherein the ethylenically unsaturated compound is selected from the group consisting of vinyl aromatic monomers, acrylate monomers, allyl monomers and mixtures thereof. 
     
     
       4. The polysulfide modified epoxy resin of claim 1 wherein the ethylenically unsaturated compound is used in an amount sufficient to copolymerize with the epoxy resin and the (vinylaryl)alkyl substituted polysulfide ranging up to about 75 percent by weight. 
     
     
       5. The polysulfide modified epoxy resin of claim 1 wherein the ethylenically unsaturated compound is used in an amount sufficient to copolymerize with the epoxy resin and the (vinylaryl)alkyl substituted polysulfide ranging up to about 25 percent by weight. 
     
     
       6. A polysulfide modified epoxy resin composition comprising the copolymerization product of an epoxy resin; a compound possessing both a group reactive with an epoxide group and a polymerizable ethylenically unsaturated group; and a (vinylaryl)alkyl substituted polysulfide. 
     
     
       7. The polysulfide modified epoxy resin of claim 6 wherein said copolymerization product additionally comprises a different polymerizable ethylenically unsaturated compound. 
     
     
       8. The polysulfide modified epoxy resin of claim 6 wherein the (vinylaryl)alkyl substituted polysulfide may be represented by the formula: ##STR9## wherein R 1  and R 2  at each occurrence are independently polyvalent organic polyradicals with each valence residing on a carbon atom; each Z is independently (vinylaryl)alkyl, inertly substituted (vinylaryl)alkyl or a non-crosslinking monoradical, provided that at least 5 mole percent of at least one Z group contains (vinylaryl) moieties; y and v are independently zero or a positive integer, x is a number from about 1 to about 8; and w is zero or a positive integer which is the difference between the valence of R 1  and two. 
     
     
       9. The polysulfide modified epoxy resin of claim 8 wherein the (vinylaryl)alkyl substituted polysulfide is used in amounts ranging from about 1 to about 99 percent by weight. 
     
     
       10. The polysulfide modified epoxy resin of claim 8 wherein the (vinylaryl)alkyl substituted polysulfide is used in amounts ranging from about 5 to about 50 percent by weight. 
     
     
       11. The polysulfide modified epoxy resin of claim 6 wherein the compound possessing both a group reactive with an epoxide group and a polymerizable ethylenically unsaturated group is selected from the group consisting of alkenyl phenols, acrylic acids, hydroxyalkylacrylates, aminoalkylacrylates, mono-esterified α,β-unsaturated dicarboxylic acids, alkenyl phenyl glycidyl ethers, glycidyl acrylates and acrylamides. 
     
     
       12. The polysulfide modified epoxy resin of claim 6 wherein the compound possessing both a group reactive with an epoxide group and a polymerizable ethylenically unsaturated group is methacrylic acid, acrylic acid or mixtures thereof. 
     
     
       13. The polysulfide modified epoxy resin of claim 11 wherein the compound possessing both a group reactive with an epoxide group and a polymerizable ethylenically unsaturated group is present in an amount sufficient to react with from about 0.01 to about 10 mole percent of the epoxide groups. 
     
     
       14. The polysulfide modified epoxy resin of claim 11 wherein the compound possessing both a group reactive with an epoxide group and a polymerizable ethylenically unsaturated group is present in an amount sufficient to react with about 0.1 to about 3 mole percent of the epoxide groups. 
     
     
       15. The polysulfide modified epoxy resin of claim 7 wherein the ethylenically unsaturated compound comprises compounds capable of copolymerization with monomers having terminal or pendant, vinyl-reactive olefinic or cycloolefinic double bonds. 
     
     
       16. The polysulfide modified epoxy resin of claim 15 wherein the ethylenically unsaturated compound is selected from the group consisting of vinyl aromatic monomers, acrylate monomers, allyl monomers and mixtures thereof. 
     
     
       17. The polysulfide modified epoxy resin of claim 7 wherein the ethylenically unsaturated compound is used in an amount sufficient to copolymerize with the epoxy resin and the (vinylaryl)alkyl substituted polysulfide ranging up to about 75 percent by weight. 
     
     
       18. The polysulfide modified epoxy resin of claim 7 wherein the ethylenically unsaturated compound is used in an amount sufficient to copolymerize with the epoxy resin and the (vinylaryl)alkyl substituted polysulfide ranging up to about 25 percent by weight. 
     
     
       19. A polysulfide modified epoxy resin composition comprising the copolymerization product of an epoxy resin containing a functional amount of ethylenic unsaturation and a (vinylaryl)alkyl substituted polysulfide. 
     
     
       20. A polysulfide modified epoxy resin of claim 19 wherein said copolymerization product additionally comprises a polymerizable ethylenically unsaturated compound. 
     
     
       21. The polysulfide modified epoxy resin of claim 19 wherein the (vinylaryl)alkyl substituted polysulfide may be represented by the formula: ##STR10## wherein R 1  and R 2  at each occurrence are independently polyvalent organic polyradicals with each valence residing on a carbon atom; each Z is independently (vinylaryl)alkyl, inertly substituted (vinylaryl)alkyl or a non-crosslinking monoradical, provided that at least 5 mole percent of at least one Z group contains (vinylaryl) moieties; y and v are independently zero or a positive integer, x is a number from about 1 to about 8; and w is zero or a positive integer which is the difference between the valence of R 1  and two. 
     
     
       22. The polysulfide modified epoxy resin of claim 19 wherein the epoxy resin contains about 0.01 to about 10 mole percent of epoxide group which have been converted to groups containing polymerizable ethylenic unsaturation. 
     
     
       23. The polysulfide modified epoxy resin of claim 21 wherein the (vinylaryl)alkyl substituted polysulfide is used in amounts ranging from about 1 to about 99 percent by weight. 
     
     
       24. The polysulfide modified epoxy resin of claim 21 wherein the (vinylaryl)alkyl substituted polysulfide is used in amounts ranging from about 5 to about 50 percent by weight. 
     
     
       25. The polysulfide modified epoxy resin of claim 20 wherein the ethylenically unsaturated compound comprises compounds capable of copolymerization with monomers having terminal or pendant, vinyl-reactive olefinic or cycloolefinic double bonds. 
     
     
       26. The polysulfide modified epoxy resins of claim 25 wherein the ethylenically unsaturated compound is selected from the group consisting of vinyl aromatic monomers, acrylate monomers, allyl monomers and mixtures thereof. 
     
     
       27. The polysulfide modified epoxy resin of claim 20 wherein the ethylenically unsaturated compound may be used in an amount sufficient to copolymerize with the epoxy resin and the (vinylaryl)alkyl substituted polysulfide ranging up to about 75 percent by weight. 
     
     
       28. The polysulfide modified epoxy resin of claim 20 wherein the ethylenically unsaturated compound may be used in an amount sufficient to copolymerize with the epoxy resin and the (vinylaryl)alkyl substituted polysulfide ranging up to about 25 percent by weight.